Patent GB-1393551-A (GB)
Title: Piperidine derivatives
IPC: C08L101/00
Filed: 1972-04-21
Abstract: 1393551 Piperidine derivatives CIBAGEIGY AG 30 March 1973 [21 April 1972 3 Feb 1973] 18558/72 and 5469/73 Heading C2C [Also in Division C3] Novel compounds of Formula I and salts thereof, wherein U is -CH= or -N=, Z<SP>1</SP> is a residue of Formula II wherein R 1  and R 2  are the same or different and each is a straight or branched alkyl residue having from 1 to 12 carbon atoms or R 1  and R 2  form, together with the ring carbon atom to which they are bound, a cycloalkyl residue having from 5 to 12 carbon atoms in the ring; X is an -O-, -S- or residue, wherein R 7  is hydrogen, a straight- or branched alkyl residue having from 1 to 20 carbon atoms or an aralkyl residue having from 7 to 12 carbon atoms; Y is -O, hydrogen, a straight- or branched alkyl residue having from 1 to 20 carbon atoms, an alkenyl or alkynyl residue having from 3 to 12 carbon atoms, an aralkyl residue having from 7 to 12 carbon atoms or the group wherein R 8  is hydrogen, or a methyl or phenyl residue; n is 0 or 1; and A is -CH 2 -, or the group wherein R 9  is hydrogen or an alkyl residue having from 1 to 20 carbon atoms; Z<SP>11</SP> and Z<SP>111</SP> are the same or different and each is a piperidine residue of Formula II as hereinbefore defined, a halogen atom, an optionally substituted amino group having the formula -NR 3 R 4 , wherein R 3  and R 4  are the same or different and each is hydrogen, a straight or branched alkyl residue having from 1 to 20 carbon atoms, a cycloalkyl residue having from 5 to 12 carbon atoms in the ring, an aryl residue which is unsubstituted or substituted by one or more alkyl groups and having a total of from 6 to 18 carbon atoms or an aralkyl residue having from 7 to 12 carbon atoms, or R 3  and R 4 , together with the nitrogen atom to which they are bound, form a heterocyclic residue having 5 to 7 ring atoms, or Z<SP>11</SP> and Z<SP>111</SP> are each independently a hydroxy or an ether group having the formula -OR 5 , wherein R 5  is hydrogen, a straight or branched chain alkyl residue having from 1 to 20 carbon atoms, a cycloalkyl residue having from 5 to 12 carbon atoms, an aryl residue which is unsubstituted or substituted by one or more alkyl groups and having a total of 6 to 18 carbon atoms, or an aralkyl residue having from 7 to 12 carbon atoms; or Z<SP>11</SP> and Z<SP>111</SP> are each independently a thiol or thio ether group having the formula: -SR 6 , wherein R 6  is hydrogen, a straight or branched alkyl residue having from 1 to 20 carbon atoms, a cycloalkyl residue having from 5 to 12 carbon atoms in the ring, or a phenyl or benzyl residue, are prepared by reacting a cyanuric halide with a compound of Formula VI and, where appropriate, with a compound of formula HNR 3 R 4 , HOR 5  or HSR 6 . The reaction is generally effected in the presence of a halogen acid binding agent and in a solvent inert under the reaction conditions. Compounds of Formula I wherein Y is hydrogen are reacted (a) with the appropriate alkylene oxide to produce the corresponding compound of Formula I wherein Y is a hydroxyalkyl group, (b) with an alkylating, alkenylating, alkynylating or aralkylating agent (e.g. a halide) to produce compounds wherein Y is said alkyl, alkenyl, alkynyl or aralkyl groups or (c) with a peroxide or a per-acid to produce the corresponding compounds of Formula I in which Y is -O. The compounds of Formula I, of which many examples are prepared or otherwise specified, are used as stabilizers in organic polymeric material, e.g. polyolefins.